


Virtual Stranger

by gwilbert



Category: The Inbetweeners
Genre: Alternate Universe - Canon Divergence, Light Dom/sub, M/M, Older Man/Younger Man, Online Dating, Sorry Not Sorry, Teacher-Student Relationship
Language: English
Status: In-Progress
Published: 2019-04-27
Updated: 2019-05-02
Packaged: 2020-02-08 11:57:13
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 7,769
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18622846
Author URL: https://archiveofourown.org/users/gwilbert/pseuds/gwilbert
Summary: Will feels depressed, ostracised and lonely. So he turns to online dating in an attempt to change all that.





	1. Chapter 1

** Virtual Stranger **

Will McKenzie was depressed.

Or at least that’s what his doctors told him.

It wasn’t a label that he felt comfortable wearing. His life was pretty decent. He was healthy, had a roof over his head and a mother who loved him dearly. But despite this, he couldn’t shake off how miserable and unfulfilled he felt, or how difficult plastering the usual awkward fake smile on his face every day was becoming.

On the sort-of bright side, his time as a state school Sixth Former was nearly over. Despite maintaining a low profile, he’d still been treated as if he were subhuman by his peers for most of the year. He’d been so looking forward to the change of pace of starting university. But sadly, the open days he’d attended so far had only filled him with fresh dread. He’d assumed that as he ascended scholastically, the cream would rise to the top and he could finally be around people like himself. Instead, he’d been met with new environments that seemed unwelcoming, and new people that he couldn’t see himself fitting in with. Indeed, university appeared to be as jam-packed full of vapid elitist dickheads as every other place of learning he’d attended in his life.

This had left Will in quite a quandary. It had always been his goal to attend a good university. So, his (quite literally) shitty performance at the previous year’s exams had been concerning. If that was how he handled the pressure of AS Levels, how was he going to cope with the countless deadlines and harsh feedback of a Bachelors course? Perhaps university wasn’t for him after all. But if it wasn’t, then what the hell was he left with as an alternative?

As usual, his precocious mentality continued to be a curse. He worried about everything and anything, past and present and future. He didn’t feel like there was anything to look forward to anymore, that life was just something to struggle through rather than to take pleasure in. His mates would often tell him to stop overthinking, to be in the moment and just enjoy things for what they were. But he found it so hard to let go, which was something they didn’t understand.

And it wasn’t as if Will could open up to them. Not in the way that he needed to, anyway. Simon was somewhat reliable in a superficial crisis, but he certainly didn’t have the capacity to process the myriad of awfulness that was plaguing Will’s mind. He couldn’t even talk to his mother, history had suggested. Any time he’d try, she’d promptly pat his shoulder and tell him that ‘everything will be alright, petal’, before scurrying off to attend to a less uncomfortable matter. And as for his father, Will was lucky to get a text back from the man nowadays, let alone be given the opportunity to pour his heart out.

This was how Will had found himself three months into a course of anti-depressants, and seeing a therapist once a fortnight. He hadn’t wanted the drugs at first. They made him feel odd, hazy and numb to everything. After a while, he realised that the numbness was preferable to misery. The drugs didn’t fix anything; all of his perceived problems still existed. He just didn’t care about them so much anymore. It was an empty sort of serenity, but serenity nevertheless.

Therapy began as a double-edged sword. Apparently, the handful of simple ‘issues’ Will had perceived himself to have were only the tip of the iceberg. The main points of discussion were usually his feelings of loneliness and disconnect, even from those closest to him. Will had come to realise how tired he was of feeling like he was from another planet, how no one in his life really understood him. Crucially, he’d realised that he felt almost pathetically desperate to form a meaningful connection with another human being, be it friendship or otherwise.

Deciding that Will was suffering from some type of social anxiety, his therapist had advised him to decide what kind of people he’d like to meet and take gradual steps towards doing so. Start small, in a safe and low-pressure environment. An online forum or chat room, for example. Engage with people he had pre-established common ground with and take things from there. Will believed that this was sensible enough advice. At least meeting people online would allow him to reign in his usual overenthusiastic quirkiness that everyone seemed to find so irritating.

So, he tentatively began signing up to websites.

Dating websites, specifically.

Gay dating websites, to be exact.

One of the very few things Will was sure of about himself was that he was attracted to both men and women. Naturally, this wasn’t something he was prepared to admit publicly. At least not yet. And it wasn’t that he was ashamed. Not anymore, anyway. But the last thing he needed was yet another target on his back, yet another peculiarity to set him apart from everyone else. And at least being bisexual gave him a ‘straight side’ to cling to, so he could at least pretend to be somewhat conventionally ‘normal’. But he also felt like he’d done nothing but fruitlessly chase after girls since joining state school. And it was getting old. So perhaps it was time to revisit the alternative, now that he was a little older. And more assured in the knowledge that he wanted more than just a frantic late-night hand-job in a creaky boarding school dormitory bunk-bed.

Despite trying numerous websites and apps, Will quickly found himself closing his accounts. Boys his age were just so fucking infuriating. Silly, unsophisticated and narcissistic. The exact reason why Will had always been more attracted to older people. They were more purposeful, more respectable, more comfortable in their own skin. When Will was younger, his father often brought business partners home for dinner. Will would sit quietly at the end of the table beside his mother, soaking in the sophisticated conversation and studying the mature noble faces around him. He liked the idea of being with someone with life experience. Someone strong-minded and authoritative. Someone to take control and ease the pressure of his own everlasting state of anxiety and indecision. Someone to balance him out, in a way.

Or perhaps it was just his percolating hormones overcompensating for his father failing to provide for him emotionally during childhood. But Will certainly didn’t want to explore that train of thought in any great detail. He already had a sizable list of ‘issues’ to work through. Some things just needed to be accepted and kept simple. He liked what he liked, whatever the underlying psychology.

Besides, it seemed he wasn’t the only one. Will had never been keen on gay porn, irked by the abundance of youthful hairless ‘twinks’ besieging every website. But one night, he dared to delve deeper. He stumbled across the ‘older on younger’ sub-genre, and his prayers were answered. Beautiful silver-haired men, self-assured and broad-shouldered, dominating their twenty-something-year-old partners. Now, this was the kind of connection he could see himself wanting! It probably wasn’t quite what his therapist had in mind, but therein lay the problem with such vague advice.

And that advice had brought Will to this point in his life; sitting at his laptop, clicking on yet another dating site sign-up link.

_‘Welcome to DaddyDating.com; virtually bridging the generation gap between younger and older men worldwide! Tell us whatever you want about yourself, although we would suggest your name, age, occupation and orientation as a minimum. A little about what you’re into and what you’re looking for in a partner wouldn’t hurt either!’_

The website name made Will cringe. He wasn’t looking for a ‘daddy’; he was looking for a partner he could connect with, in mind and body. Incestuous phraseology aside, he set about completing the profile information. He entered his usual pseudonym, ‘Billy’; he’d never felt comfortable using his real name for things like this. The site was age-restricted, understandably. Will wasn’t 18 quite yet, but would be in a few months. He figured he’d boost his age up a couple more years for good measure though. It wasn’t as if he acted or even looked like your typical teenager, and saying he was in his twenties would hopefully filter out any paedophilic weirdos.

A quick glance at other profiles on the site told Will that when they asked for what members were ‘into’, they weren’t referring to hobbies and interests. Given Will’s sexual experience – or lack thereof - this could be a tricky question to answer. He wanted to get this right though, so he tried to be as honest as he could without sounding like a total turnoff. Naturally, he rewrote the damn thing multiple times over. He wanted to sound mature, but not joyless. Mindful, yet casual. Approachable, but not easy. Was such a combination even possible?

After about an hour of agonising over every word, Will finally sent his profile live.

_‘Hello. My name is Billy. I’m 21 years old and I’m a Literature & Journalism student from Watford, UK. I’m attracted to both men and women. I explored my ‘gay side’ a bit when I was younger, but clumsy fumblings with my peers didn’t really hit the spot for me. Men my age are intolerable, quite frankly. I’d say I’m rather submissive, but other than that, I’m not entirely sure what I’m ‘into’ yet. I’m somewhat of a late bloomer, I suppose. Hence, I’m looking for an older man to introduce me to new experiences and teach me how to do things properly.’_

It wasn’t long before he started receiving messages. Some of his suitors were as young as 35, others as old as 60. Most of them shared one thing in common though; they were only looking for a hook-up. Some were quite aggressive in their approach, immediately sending intimate photos or asking for a phone number. Others used terminology or acronyms Will wasn’t familiar with, or asked questions he didn’t feel comfortable answering. The usual feelings of isolation started creeping in, and he quickly felt out of his depth.

Just as he was about to admit defeat and delete his account, he noticed a new message in his inbox from someone calling themselves ‘Greg’. Morbid curiosity got the better of Will, and he clicked the message open.

_GREG: ‘Well, this is a refreshing change. Seeing a member of the younger generation using proper sentence structure on this godforsaken site is quite the rarity. Kudos to you, Billy.’_

Will felt his the knot in his stomach unclench. Talk about a refreshing change! This message was the polar opposite to all the rubbish he’d been receiving thus far. Curiosity peaking, he clicked open the other man’s profile. ‘Greg’ was relatively new to the site, signing up less than a month previously. Not unlike Will, he hadn’t uploaded a photo of himself yet, but his profile was pretty informative.

_‘Greetings! I’m Greg, a 42-year-old prison officer from Watford, England. As much as I despise these arbitrary modern labels, if a gun was held to my temple, I would describe myself as bisexual. As a keen authoritarian, my aim is to meet a younger man who is both willing to learn and eager to please. I’m not overly hung up on looks, as heaven knows I’m no oil-painting myself. However, intelligence is a must and morons need not apply. I’m quite serious on this point. If you’re the type of person who enjoys ‘reality TV’ or uses emoticons unironically, do not bother contacting me.’_

For the first time in a while, Will felt himself smile genuinely. Greg seemed right up his street. Cynical, witty, commanding. And not too old. Well, old-ish. The man was literally the same age as his own father. Twenty-five years his senior, for goodness sake. A whole quarter-century older! The numbers were actually quite staggering, when he really thought about it.

Will’s eyes washed back over Greg’s profile description and he felt any voices of doubt begin to quell. And there was no harm in just having a chat. This was what he was here for, after all. He thought for a moment, then typed a reply.

_BILLY: ‘Thank you, Greg. Your message is also a welcome divergence from the norm. The number of Neanderthals hounding my inbox has been rather eye-opening. And not in a good way!’_

Less than a minute went by before a reply came through.

_GREG: ‘I can quite imagine. Incomprehensible drivel accompanied by unsolicited penis pictures?’_

_BILLY: ‘Add an obscene sense of entitlement to my personal information to that list, and you’re 100% correct!’_

_GREG: ‘Typical. Animals. So, other than your dissatisfaction with clumsy fumblings, what brings you to this site?’_

_BILLY: ‘To be honest, this is the first time I’ve signed up to something as… specific to my needs as this? I think I’ve always preferred the company of people older than me though. Especially men. So it made sense to give it a try. How about you?’_

_GREG: ‘A similar story. I’ve tried dating women and men my own age with little success. Nobody holds my attention for long. I get bored with people generally, let alone romantic partners. Don’t let that discourage you though.’_

_BILLY: ‘Not at all. I’m the same way, truth be told. So you thought you’d try seeing someone younger?’_

_GREG: ‘A friend of mine convinced me to keep an open mind towards it. He assures me that you young’uns are more vibrant and interesting than folk our age. I just thought he was a dirty old perve at first. But as the popular saying goes, don’t knock it ‘til you try it.’_

_BILLY: ‘Absolutely. And have you tried it thus far? If you don’t mind me asking?’_

_GREG: ‘I don’t mind at all. Thus far, I’ve had a few extremely unsuccessful ‘dates’. Young men may be more vibrant but, as you so aptly point out in your profile, they are also very fucking tedious.’_

_BILLY: ‘Quite! I don’t know how you can stand to entertain people my age, male or female. In my experience, most of them are infantile vain twats.’_

_GREG: ‘Yes. It does seem to be rather a conflict of interest, to desire that a mature mind come housed in a not-so-mature body. I’d been holding out for a diamond in the rough. I was starting to give up hope.’_

_BILLY: ‘It’s funny you should say that. I was losing faith in finding someone on this site that wasn’t a total degenerate. I was literally about to delete my profile before you messaged me.’_

_GREG: ‘Well, I hope I continue to restore your faith.’_

_BILLY: ‘And I hope I continue to keep your attention.’_

The chat continued to flow with remarkable ease. Greg came over as outspoken, intellectual and mordant; all traits that Will admired. They had a similar sense of humour, and numerous things in common; a fondness of reading, 80s music, walks in the countryside, quiet pubs, and a general dislike of being around people. And much to Will’s surprise, Greg had earned a combined Bachelors in History & English in his younger years before moving into probation services. Greg told Will a little about his role as a prison officer, describing some of the inmates he particularly disliked. As much as he hated to lie, Will briefly talked about his make-believe degree. It was really only sort of a lie anyway. He would hopefully be a Bachelors student before long. And other than this one little fib, he stayed as true to character as possible. Without allowing himself to go too overboard, of course.

Will actually couldn’t remember the last time he’d had so much fun talking to someone. In fact, he was having such a great time that he had to keep reminding himself to remain guarded. Greg seemed wonderful, but he was still an older stranger. It would be foolish for Will to give away too much information about himself at this early stage. In fairness, Greg didn’t ask for anything particularly personal despite hours of talking. Not even a photo, which was often the first thing people asked for on sites like this. Perhaps he’d noted Will’s displeasure at other men doing this and had decided not to. Or maybe Greg genuinely wasn’t concerned about looks. Either way, it was very courteous of him, and Will rewarded this courtesy by volunteering a description of himself in lieu of a picture. Greg responded in kind, describing himself as ‘clearly middle-aged, tall, grey and a body like a badly-made bed’. Will wasn’t even remotely put off. One thing state school had taught him was that looks were very much only skin-deep, since most of the conventionally attractive pupils were about as deep as a papercut. He’d gladly take good conversation over a pretty face any day.

It was close to four in the morning when Will reluctantly excused himself from the chat, saying that he had an ‘early lecture’ but would contact Greg again as soon as he could. Over the days that followed, they continued to chat for hours at a time, and Will found himself liking Greg all the more. He admired the older man’s intelligence, directness, and his delightfully acerbic wit. In turn, Greg seemed to appreciate Will’s high-brow attempts at humour that would often fall flat with his peers. He would remark favourably at how articulate and profound Will could be, and Will couldn’t help but savour even the smallest compliment. And he never felt pressured to act ‘cool’ or ‘normal’ when talking to Greg. He could just be himself. Even though he was currently just words on a screen, Will’s new friend had him pretty smitten. And he hoped Greg was feeling the same.

On occasion, their conversation would turn to sex. It started when Will asked Greg to elaborate on what ‘keen authoritarianism’ involved. Greg gladly explained the ‘Dom-Sub’ dynamic; where the dominant party derived gratification from coaching their trusting submissive, who in turn would gain pleasure from serving their coach. It sounded like an ideal scenario. In Will’s view, having someone to guide you through the minefield that was sex could only be a good thing. He also loved to learn, and to try new things, within reason. And he was, of course, a perpetual approval-seeker.

Spurred on by Will’s interest, Greg delved more into the sexual side of the dynamic, giving examples of what might occur between them, should they meet up. It was nothing too obscene. In fact, most of it sounded amazing. However, some things seemed a little rich for Will’s tastes. For instance, he quite liked the thought of being spanked, but balked at the mention of a belt or cane. And being tied up sounded like it could be fun, although the idea of being blindfolded made him rather uncomfortable. Perhaps that was the point though; to help the submissive to become comfortable with the uncomfortable. It was an intriguing concept; one he definitely wanted to research further.

When Greg asked about his own experience with past partners, Will didn’t shy away from the question. Lying about his sexual history had never done him any favours in the past. So he simply told the truth; that other than heavy petting, he hadn’t really done much of anything. Greg didn’t seem bothered by his virgin status, which was reassuring. So reassuring, in fact, that Will felt safe to open up about his intentions.

_BILLY: ‘To be frank, I was sort of hoping to change that as a result of using this site.’_

_GREG: ‘I’m rather surprised by that. Pleased, but surprised.’_

_BILLY: ‘How come?’_

_GREG: ‘Considering how well we’re getting along, do I really need to explain why I would be pleased?’_

_BILLY: ‘Ha! I meant, why is it surprising?’_

_GREG: ‘You just strike me as the kind of lad who would aim for the illusionary objective of wanting their first time to be special.’_

In a way, Greg was right. Will used to romanticise sex, aspire to special. But his goal to lose his virginity whilst also embroiled in a meaningful relationship always seemed to be at cross purposes.

_BILLY: ‘In an ideal world, I would. But as you say, it’s fantasy. I mean, how many people can hand-on-heart claim that their first time was truly special? My first girlfriend already had eleven lovers under her belt (literally!) when I met her. Not that there’s anything wrong with that, but how many of them were genuinely special to her? What does ‘special’ even mean, anyway? Sorry, I’m rambling again.’_

_GREG: ‘Not at all. You raise a good point. ‘Special’ is rather a hollow and asinine term to describe a sexual experience. Or any experience, for that matter.’_

_BILLY: ‘Exactly. I’d much rather base my decision to lose my virginity on logic and reason than hazy sentimentality. Besides, most men I know are just trying to stick it in anyone, as if they’re just trying to get it ticked off their to-do list as quickly as possible.’_

_GREG: ‘So for you, it’s just a case of following the other lemmings off the cliff’s edge and getting it over with?’_

Will quirked an eyebrow in amusement. Typical Greg. Sardonic and to the point.

_BILLY: ‘Not at all. In fact, I’ve been presented with a few opportunities to just ‘get it over with’. I haven’t taken them because it didn’t feel like the right thing to do. But I’ve thought it over, and I’ve decided that ‘special’ is overrated. I don’t need moonlight or rose petals or ‘the one’. Just someone that I feel comfortable enough with that the likelihood of me regretting it on my deathbed is somewhat reduced. That would be ‘special’ enough, I think.’_

_GREG: ‘Well, nobody could fault you for having realistic expectations.’_

_BILLY: ‘Lofty ones give me acrophobia.’_

_GREG: ‘Ha! Hopefully when we meet, you’ll find yourself feeling comfortable enough with me. I’d be honoured to tick your list.’_

Will’s heart skipped a beat at this prospect. The idea of giving his body over to a stranger had never appealed to him in the past. In fact, it downright frightened him. So why was the idea of being with Greg so enticing? Perhaps he didn’t consider Greg a stranger anymore. Granted, they hadn’t met in person, spoken on the phone or even seen each other’s faces yet. But that didn’t alter the fact that Will felt as if he could bare his soul to this man. It felt so good to feel that way about someone. And if feeling that way made him stupid or naïve or crazy, so be it.

_BILLY: ‘I think I’d like that.’_

_GREG: ‘Is that so?’_

_BILLY: ‘Yes. I’ve thought about you a lot today.’_

_GREG: ‘Oh? What kind of thoughts?’_

_BILLY: ‘The kind that made me want to abandon my lecture and find somewhere to be on my own. The kind that only a warm hand or a cold shower could fix.’_

_GREG: ‘Go on.’_

Will started to feel slightly flustered, but breathed deeply and pressed on.

_BILLY: ‘I thought about the things you’ve told me about submission and how perfect it sounds for me. About how it could be exactly what’s been missing in my life. But mainly, about how much I want to succumb to your guidance and prove how good I can be for you.’_

_GREG: ‘Those all sound like very intense thoughts, my young friend. However did you deal with them?’_

_BILLY: ‘The same way I always do. Stripped bare, I lay back on my bed and feel the sheets cooling my skin. I close my eyes, letting every thought and fantasy of you flood my brain. With every shameless touch to my hot flesh, I wish more and more that you were there, steering my hand. And I reach sweet release with your words on my mind and your name on my lips.’_

Will’s cheeks were undoubtedly red by the time he hit the send key. He wasn’t exactly used to talking like this, but was definitely getting better with practice. As always, there was a pause as Greg ‘absorbed’ his message.

_GREG: ‘Beautiful, my Billy. Sensuous and lyrical. You have such a way with words.’_

Will’s smile burned brighter than his face.

_BILLY: ‘I’m glad you enjoyed it. I hope I can be as poetically uninhibited for you in person.’_

_GREG: ‘We’ll find out soon enough, love. And you’re not alone in your thoughts. I’ve been thinking about you too. Every night since we first started talking, in fact. I’ve laid awake, imagining all the things I’d be teaching you if only you were there with me.’_

_BILLY: ‘What kinds of things?’_

_GREG: ‘I’d teach you how to fully give yourself over to my authority. How to appreciate my firm hand of guidance. And how to bring to life sensation that others only dream of.’_

_BILLY: ‘And do you imagine me being a good student for you?’_

_GREG: ‘I imagine quite a lot about you. I imagine you keen and waiting on your knees at my feet. Your body draped elegantly across my lap. Or sprawled out and whimpering in desire on my bed. But whatever your position, yes. You’re always exceptional.’_

Suddenly feeling like he hadn’t breathed in a while, Will inhaled shakily. He gently tugged at the material of his pyjama bottoms, giving his hardening cock some space to move.

_BILLY: ‘What wonderful thoughts to be having.’_

_GREG: ‘Yes. It’s just a shame I don’t have a face in mind to fully facilitate them.’_

A cringe marred Will’s contented expression. He had seriously considered sending Greg a picture of himself a number of times in the past few days. But the fear of rejection and a cynical internal voice of mistrust always stopped him. This time was no different.

_BILLY: ‘I’m sorry. I just don’t feel comfortable putting my face on these kind of sites.’_

_GREG: ‘My apologies, I didn’t mean to suggest that you should. I just meant that I’m keen to see you.’_

Relieved, Will allowed the smile to return to face.

_BILLY: ‘Same here. And I’ll gladly send you all the pictures you want once we’ve met in person.’_

_GREG: ‘You’d just like to confirm that I’m not some crazed axe-murdering human-trafficker first?’_

_BILLY: ‘Ha, yes! It’s not that I think you might be, or that you might do something weird with my picture. I’m being overly cautious, I suppose.’_

_GREG: ‘Not at all. In fact, you may have noticed that I’m rather the same way. You never can be too careful. Especially in my line of work.’_

_BILLY: ‘Exactly. I’m glad you understand.’_

_GREG: ‘I certainly do. Believe me. When you have a face like mine, you’re never too thrilled to be in front of a camera.’_

_BILLY: ‘Now, don’t sell yourself short! If looks were to match personality, I’d care to bet that you’re very handsome indeed.’_

_GREG: ‘I appreciate your hopeful sycophancy, dearest Billy. But be warned. You’re talking to a regular Joseph Merrick here.’_

_BILLY: ‘Ha! Oh, come on! You’re just being modest!’_

_GREG: ‘Well, I suppose I do have this going for me…’_

An offer to file-share popped up in the message box. Will hesitantly accepted and was awe-struck by what he saw. A large semi-erect penis with a silvery halo of pubic hair filled his laptop screen. Will blushed, a chill running up his spine as thoughts of what he could do with a cock like that flooded his mind. At a guess, it was around seven inches and generously girthy. Would something that size even fit inside him?

He snapped out of his stupor, realising he’d been silent for quite some time.

_BILLY: ‘Wow.’_

Not exactly Shakespeare, but he was genuinely lost for words. Greg replied instantly.

_GREG: ‘Indeed. Care to return the favour?’_

Apprehensive, Will stared at the screen. He’d always held the position that sending dirty pictures was ridiculous and pathetic. But as much as he didn’t want to be a hypocrite, he also didn’t want to disappoint Greg. And at least his cock, unlike his face, was unidentifiable.

_BILLY: ‘I suppose it would be rude not to. Just a second.’_

He reached for his phone and shifted in his seat, hitching his pyjama pants down a little way. His own five-inch length was almost fully erect, due to both their naughty conversation and feasting his eyes on Greg’s offering. It took him three attempts to get a decent shot, hands shaking with adrenaline as they manoeuvred the camera, but Will found himself pleasantly surprised at how flattering the final picture turned out.

He took a moment to breathe as he blue-toothed the photo to his laptop. Part of him was screaming that he shouldn’t be doing this, but the rest of him was relishing the rush of his mischief. He sat waiting in nervous anticipation as Greg accepted his file-share request. It didn’t take him long to respond, but every passing second made Will’s heart thud harder.

_GREG: ‘I’m afraid it’s rather hard to pass comment. Your camera’s resolution is woefully inadequate.’_

Will’s face burned hot at that.

_BILLY: ‘My apologies.’_

_GREG: ‘No bother. There’s more than one way to skin a cat. For instance, I would suggest that we meet up sooner rather than later. That way, I can offer you a full and frank appraisal in person.’_

Hands freezing where they were poised over the keyboard, Will felt his stomach flutter. Suddenly, it felt like things were moving rather fast. They’d only been talking just over a week. Fair enough, they’d talked a lot in that time, but still… Was it too soon to be meeting up?

When he thought about it though, a week was probably a snail’s pace by today’s standards. Lads at school often met up with girls they found on dating apps within hours of making first contact. Greg seemed to be genuine, and was on Will’s wavelength. And they would have to pull the trigger on a meet-up at some stage, wouldn’t they? Or else what would be the point?

Will’s fingers met the keys once more.

_BILLY: ‘Sounds enlightening. When were you thinking of?’_


	2. Chapter 2

They arranged to meet that following evening, a Thursday, at a quiet bar on the outskirts of London. It wasn’t a gay bar, strictly speaking. But it was in a gay-friendly area with many gay-friendly businesses surrounding it, including a nice little B&B. Will had tentatively agreed to Greg’s suggestion that they book a room there for the night. This agreement came amidst promises from Greg that he, in his role as a responsible Dom, would never push his Sub into anything they weren’t ready for. Whether he wanted to merely talk the night away or go the whole hog, Greg swore that he’d go along with Will’s decision. And for whatever reason, Will had faith that the older man would honour this promise.

Will had told his mum that he’d be spending the night at Simon’s so that they could make some headway into an important Sociology project. Luckily, she bought it without question and didn’t make any issue of him staying out on a school night. As luck would have it, Will didn’t have any classes until after morning break on Fridays. So at least he’d have time to get home and wash away the sin after his mum had left for work.

The hours leading up to Thursday evening flew by. He’d barely said a word all day at school, too caught up in his own head to engage in coherent conversation. To be fair, his friends were probably grateful for the peace and quiet. It wasn’t as if he could talk about what was on his mind anyway. They didn’t even know he swung both ways yet, let alone that he arranged dates with middle-aged strangers off the Internet. Part of him was relishing in his secret though, and longed to see the looks on their faces if he were to spill the beans. It was so unexpected of him, to do something so outrageous. They’d never suspect that prim and proper Briefcase would have the balls to pursue his heart’s desire so fearlessly.

Perhaps ‘fearlessly’ wasn’t quite the right word. He was shitting himself more than just a bit over having committed to doing something so reckless. In fact, it was safe to say that his sensible side was having a full-blown meltdown.

_‘Seriously, what the fuck have you gotten yourself into? See, this is what happens when you take mind-altering drugs! That Citalopram has majorly fucked you up! I thought you wanted to be normal! This isn’t normal! This is insane! You can’t meet some random strange old bloke, you fucking idiot! What if he’s a nutter or some sort of sexual predator?! You could end up raped or worse! You shouldn’t do this! Scratch that - you **can’t** do this! You simply cannot do this!’_

But despite his apprehension, he couldn’t silence the contradictory voice pushing him onwards.

_‘Look, Greg seems really nice. You’ve never connected with someone quite like this before. And you trust him as much as you can realistically trust a man you’ve never met in the flesh. Take a chance, for once. Yes, it seems scary and risky. But that’s what taking a gamble is about. And of course, there’s a chance that he might not turn out to be all you’re hoping for. But the opposite could be true too. You’ll regret it forever if you don’t at least try. Stop overthinking. Just go with what feels right.’_

And what ‘felt right’ to Will was to board a bus headed for the outskirts of London.

He deliberately arrived at their rendezvous point half an hour early in order to build up some much-needed Dutch courage. The bar was lovely. Tasteful, cosy and quiet, just like Greg had described. Will ordered a glass of red wine for himself, and a double measure of neat Jack Daniels for his date. Thankfully he didn’t get carded, so either the bartender didn’t care or the effort he’d put into his appearance had paid off. Greg had asked that Will make himself distinctive by sitting in a corner booth reading a book, so that’s what he did. He’d brought his copy of ‘The Canterbury Tales’; always a good go-to when trying to impress people with his aptitude for reading. But when he tried to focus on the pages in front of him, all the words seemed to blur together. Apparently, his literacy skills went out of the window when he was nervous and horny.

Abandoning his book, Will sipped his drink as he ran a mental inventory of the preparations he’d undertaken earlier on. Said preparations had gone beyond ensuring that he was clean and tidy for a potential sexual encounter. His sensible side, fully expecting the situation to go awry, ensured that he’d hidden some cash and taxi numbers in his sock, and a discreet rape alarm in his trouser pocket. He’d also placed a note under his mattress, giving the address and time of the meet-up. If the worst happened, Mum would find it eventually and could offer the police some form of lead. It was a morbid way to think, but Sensible Will knew that it was better to be cynical than sorry.

Reckless Will, on the other hand, had been more concerned that he’d dressed to look the age that he’d claimed to be. Of course, this didn’t change the reality that he was currently still a teenager. Will actually felt rather guilty about the fibs he’d told online. Greg always talked about how trust was paramount for him in a relationship, and Will had decided that he needed to come clean before they went any further. In fairness, his age and his present role as a student was all he’d really lied about. And his name. Otherwise, he’d been entirely true to himself. If the situation were reversed, Will felt he could overlook a fib or two on Greg’s part if they turned out to be just as compatible in person. Hopefully, Greg was the forgiving kind. It was too late to turn back now anyway. Will just had to keep his fingers crossed that luck was on his side this time.

Before he knew it, 9pm was moments away. Will toyed with his wineglass, swirling the cherry-red liquid around, feeling oddly soothed by it. He wasn’t entirely sure if he should be drinking alcohol with his medication on board. It was probably a bit late to be having thoughts like that since he’d nearly finished the glass. One was probably his limit tonight. Heaven forbid he embarrass himself by throwing up. Or shitting himself in public, again. Or even-

“Well, isn’t this unexpected?”

The familiar voice of the person who had appeared by his booth registered instantly. Panic began to set in as Will looked up to meet the stony eyes of the last person he’d expected to see tonight.

“Mr Gilbert?! What are you-? Why are you-?”

“Shut up, McKenzie.”

With a scornful shake of his head, the towering Head of Sixth slid into the opposite side of Will’s booth. He was wearing smart-casual jeans and blue plaid shirt, a dramatic contrast to his usual formal attire. His hair was neatly combed back, and an invisible cloud of balsamic aftershave lingered in the air around him. These observations did nothing to help Will as he scrambled for an excuse. Any reason he could give his teacher for him being there, on his own, so far from home, so late in the evening. As Will fumbled, Gilbert picked up his discarded book and flicked through it carelessly.

“So… how’s the hectic world of Literature and Journalism treating you?”

It took Will a moment to process this question. At first, it confused him. Then, as reality sank home, it horrified him.

“What? No! Oh, no…”

“And congratulations on turning 21. Had I known, I’d have sent you a greetings card.”

His sarcastic barb falling on deaf ears, Gilbert tossed the book back down onto the table and snatched up the whiskey glass. He took a long glug of bourbon, glaring at his pupil’s wide-eyed dismayed face. Eloquent as he was, Will couldn’t conjure the words to describe how mortified he felt. His stomach churned as he thought of all the private matters he’d discussed with ‘Greg’, all the intimate exchanges they’d had. The exchange of certain intimate photos, in particular!

After savouring the mouthful of liquor, Gilbert stared his young companion down sternly, eyebrows raised. Will knew that look well, and dutifully settled in for the bollocking he was about to receive.

“Tell me something, ‘Billy’. What exactly was it about venturing miles from home to spend the night with a middle-aged stranger that screamed ‘this is a good idea’ to you? We both know you’re not stupid and you can’t possibly be that fucking naïve. So I can only assume that you’ve finally lost what tenuous grip you’ve previously held onto your sanity by.”

That touched a nerve. A nerve so sensitive that it instantly snapped Will out of his dumbfounded timidity.

“I haven’t lost anything!” he said sharply. “This was…it was just something I felt that I wanted. Something I thought that I needed. I took a chance and of course, it backfired. It went horribly wrong, just like everything else in my life.”

“Oh, cry me a river!” Gilbert scoffed. “You’re not the only one suffering here. I thought I was meeting up a witty bookish twenty-something, not some precocious little shit looking to catfish a surrogate father figure.”

“‘Catfish’?” Will frowned, indignant. “I don’t believe I’m the only one who’s been deceptive here, ‘Greg’. How were the inmates today, hmm? Shake down any cells? Witness any shankings?”

He gulped, throat drying as the teacher’s eyes narrowed at him. It was rare for him to speak out of turn with his elders. But whether it was down to his meds, the Shiraz or the emotional intensity of the situation, he just didn’t feel as intimidated by the menacing giant as he usually did.

“‘Gregory’ is my middle name.” Gilbert said evenly. “And you elevating your age into adulthood is on a much higher level of deception than me bending the truth about my occupation. It’s not that radical of an exaggeration anyway. You know as well as I do, that lunatic asylum makes Broadmoor look like fucking Disneyland.”

“Nothing to do with the potential stigma associated with an educator meeting young men online for sex then?”

“You want to talk about stigmas, do you? Okay; what stigma is there associated with a 17-year-old boy seeking out the answer to all life’s problems down the shaft of a middle-aged man’s penis? Can you say ‘daddy issues’, McKenzie?”

Will bristled, but kept his composure. “First of all, I don’t appreciate you continually mischaracterising me as a child. By legal definition, I’m of age. Secondly, I’m free to seek out whatever kind of penises I like. Whether they’re my age, middle-aged or fucking geriatric, that’s my own business. Finally, I would reiterate that you are a secondary school teacher with an appetite for younger men. You’re hardly in any position to be judging me or my so-called ‘issues’, are you?”

Gilbert was unfazed. “Legally speaking, you are indeed free to choose who you sleep with. As am I. However, the fact remains that the choice you made in coming here tonight had massive potential for disaster. Not least because you’ve lured someone here under false pretences.”

“False pre-?!” Will trailed off with an exasperated snort, reaching for his wineglass. “Whatever!”

“And while you might be of age for consent, might I remind you that you are not yet old enough to purchase alcohol legally?”

“Oh, shut up, will you?” Will snapped. “What is this, exactly? Is this you trying to be my ‘daddy’? Are you going to tell me what a naughty boy I’ve been and put me over your knee? Well, this isn’t your office. So kindly shut the fuck up and let me drown my sorrows. You have no jurisdiction over me here, **Phil**.”

With that, he pointedly took a lengthy draught from what remained in his glass. To his surprise, Gilbert didn’t retort. He simply sat there, studying Will’s defiant face. He wasn’t utilising his customary death-glare either. More of a wistful gaze, his eyes lingering on the teen long enough that it made Will feel quite unnerved. He then smirked, raising his own glass as if toasting.

“Indeed I don’t.”

Having downed what was left of his whiskey, Gilbert rose from the table.

“Shall we, then?”

Will scowled up at him. “‘Shall we’ what?”

“Well, seeing as you’re determined to have some decrepit pervert violate you, you may as well surrender the privilege to one who isn’t likely to leave you dead in a gutter afterwards. Although I make no promises.”

Gilbert gestured behind himself. Will followed the movement with his eyes, out of the window and across the street. To the bed and breakfast where ‘Greg’ had booked them a room. The penny finally dropped. Will’s eyes widened.

“You’re not suggesting that we actually-?”

“What I’m suggesting,” Gilbert interrupted. “Is that we both have needs that the other is capable of satiating. I can serve as a filler for that father-shaped hole in your heart, and you can be your usual virtuous complaisant little self for me. Sound fair?”

After a moment of astonished silence, Will let out a short derisive laugh.

“In theory, ‘Greg’,” he replied caustically. “Except for one minor detail; you’re my Head of Year.”

The teacher shrugged. “Not for much longer.”

“You’ll still get struck off if we’re found out!”

“I’m quite aware of that. I’m sure I’ll be able to count on your discretion as much as you can count on mine.”

Will gaped helplessly. This was fucking absurd.

“But… Still, if-”

“It’s not your concern, McKenzie. So if your only reservations are in relation to my livelihood being in jeopardy, then-”

“Oh, believe me! I have other reservations!”

“About?”

“Tomorrow morning, for starters!”

“What about tomorrow morning?”

“Tomorrow morning! When life goes on! When you’re back in your suit, I’m back in my blazer, and we have to pretend like we haven’t spent the evening playing master-slave!”

Will cringed as the words left his mouth. Gilbert, on the other hand, looked quietly thrilled at the prospect.

“If it makes you feel any better, consider it an extracurricular activity,” he breathed. “Based on the conversations we’ve had over the past week or so, you’re open to being educated in such a manner. Correct?”

Other than a conflicted expression, no reply came.

“I suggest that we finish this discussion in private.” Once again, Gilbert nodded towards the neighbouring building. “Join me, or don’t. Choice is yours.”

Tearing his eyes away from the older man’s, Will breathed deeply and began gathering his thoughts. It would, of course, be totally inappropriate to have any sort of sexual encounter with his teacher. But maybe that inappropriateness was what was making the idea seem so tempting. In all fairness, Will had received exactly what he’d asked for; a dominant older man who he could trust with his body. And the fact that Gilbert wasn’t a total stranger certainly removed some of the aforementioned danger from the situation. Theoretically, anyway.

Will’s eyes flickered back over to his teacher, who was still watching him expectantly. Maybe it was the drugs or drink talking, but Gilbert was unexpectedly easy on the eyes in his casualwear. He was even rather handsome, at a push. Come to think of it, he didn’t look too bad in his suits at school either. And Will had already received a memorable preview of what lay beneath those clothes.

More significantly - to Will, anyway – he’d genuinely liked the person he’d spoken to online. Perhaps Mr Gilbert - Phil - was different outside of his professional role. Perhaps the connection they’d formed was real. It wouldn’t be fair to deny themselves exploring the relationship further, simply because their paths had already crossed in life. Perhaps Will didn’t want to let go of ‘Greg’ just yet.

Or perhaps he was just scrambling for any excuse to see that incredible-looking cock in person.

Either way, his mind was made up. With a nod, he downed the remaining wine in his glass and shakily rose from his chair.


End file.
